Waukesha, Wisconsin – A Small Town that Gives You a Big Wisconsin Vacation

Big name cities are enticing and they certainly can offer endless opportunities when it comes to travel experiences. Sometimes it is their neighboring little brother, while not having all of the glitz of their big brother, has something more unique and memorable to offer. That is exactly what you get when you visit Waukesha, Wisconsin.

Waukesha is just a short drive from Milwaukee and a slightly longer drive to Madison and although Green Bay is a little further that both of those, it is still a reasonable path to get to TitleTown. While ideally situated to visit any or all of those cities while staying in Waukesha, there really is no need to leave. You can enjoy an entire vacation within this quaint city.

Les Paul Inspired Artwork Throughout Waukesha

Every city it seems has that one icon that grew up in their city and that city always takes pride in sharing that name and history with the world. For Waukesha, that man is the late and legendary Les Paul. While his role in developing the solid body electric guitar, Les was simply an electronics genius. You don’t have to be a guitar aficionado to visit the Waukesha County Museum and learn more about Les. Obviously known across the world when it comes to his role in the world of guitars, the museum takes you through the creations he started as a young boy and then takes you through his entire career including clips of what very well could be the first reality show on television, that took you into the home of Les and his wife Mary Ford, “Les Paul & Mary Ford At Home”.

Les Paul Section of Waukesha Museum

Club 400 located downtown Waukesha, while a longtime popular bar, also doubles as a shrine to Les. The now iconic bar was at one time was owned by Les’s father and brother, George and Ralph Polfuss. Thankfully in 1981 the bar was purchased by Dan Pokwinski, who not only kept the bar going with the small-town, friendly appeal, but he realized what Les meant to Waukesha and you will find the history of Les throughout the bar. If you happen to catch Dan behind the bar, you can hear him glowingly talk about the many times Les came back to Waukesha and how he would make it a point to stop at Club 400. Club 400, a historical landmark, is one place you must visit, not only to stand in the very bar Les used play in, but also to get a sense of the warmness that a classic bar like this has to offer. Les was so much more than a guitar and Waukesha is a city that loves him as much as he loved it and it is well worth your time to walk in his footsteps and learn a little more about this amazing man.

Dan Pokwinski inside of his Club 400

What might be the most singular interesting spot in Waukesha County is Ten Chimneys, which is located more specifically in Genesee Depot. Ten Chimneys literally takes you back in time and that is no exaggeration as nothing has been changed giving it the appearance of still being lived in since it has been opened to the public in 2003. Ten Chimneys was the home to Broadway legends Alfred Lunt and Lynn Fontanne.

Scenic Ten Chimneys

If you are not familiar with Alfred Lunt and Lynn Fontanne, this is a story that you will love of not only an incredible couple, but also who were considered the premiere acting team on the English-speaking stage. To tell you a little bit about Alfred and Lynn and what they meant to each other and what Ten Chimneys meant, they had two requirements in their contract, first, the Lunts insisted that they only act together, rather than in separate plays and second that they would never act in the summer, so they could instead come to Ten Chimneys.

Ten Chimneys is a tour that you will not want to rush through and in fact once you begin seeing it you will be so drawn into the history, beauty and that you will lose track of time. It makes no difference of where you come from, who you are or your age, anyone who visits Ten Chimneys will be in awe of the life that was created in middle of seemingly nowhere. In addition to the tour itself, Ten Chimneys hosts some amazing people to perform at the active venue. In March of 2017 Olympia Dukakis will be taking the stage.

When it comes to unique experiences, you are going to have to travel pretty far to find anything like Veloce. Veloce might fall under the category of a go-kart experience, but it is far beyond that. This incredible indoor track is home to an Italian Electric Kart Speedway. These go-karts might just cost more than your car and go nearly as fast, up to 50 miles per hour. This is an amazing experience for anyone who loves speed!

Veloce Indoor Go-Kart Racing

This is Wisconsin so we can’t go any further without a mention of beer. While the state is home to a number of breweries, Waukesha recently became home to a newcomer to the beer industry, Raised Grain Brewing Co. The motto of Raised Grain is “Boldly Brewed Beer” and they live up to that, creating unique flavors and bringing out the most flavor imaginable in each beer. Raised Grain is home to a beautiful handcrafted tasting room that was created with reclaimed timber from A.J. Pietsch Co., better known as the woodworking shop immortalized on the Old Streets of Milwaukee exhibit. Raised Grain has already taken home awards for their beer, despite such a short existence. If you like a dark and rich beer, the black walnut will satisfy you completely, as this is a perfect Belgian Imperial Stout.

Raised Grain Brewing Company

You could create a show on the Food Network just making your way through Wisconsin and visiting every little hole-in-the-wall restaurant that every city seems to have and love. If you are in Waukesha two words seem to make everyone’s eyes light up and those are ponza rotta. You are only going to find a ponza rotta in downtown Waukesha at Jimmy’s Grotto. Simple and unpretentious, you walk up to the register and place your order and wait for what can be best described as a combination of a deep fried calzone was joined at the hip with a giant mozzarella stick. Whatever ingredients you choose from the lengthy list of pizza toppings, you can trust you will not be cheated. One slice into the crispy and flaky dough and cheese just oozes out. If you are going to eat one thing in Waukesha it has to be a ponza rotta and trust me you will never forget the name after you have tried one.

Every region of the country has their burger that has risen to iconic standards such as on the west coast In n’ Out can do no wrong. Well while Waukesha isn’t the only place you can find a Culver’s, its roots are tied to the Midwest and no matter where you are, if you come across one, stop. The butter burger will put up a battle against any other burger when it comes to the question of “what is the best burger around”? If you giving you an incredible juicy and tasty burger wasn’t enough, Culver’s gives you the delicacy of custard.

The Culver’s Butter Burger

Small town America seems to be fading from the landscape and that isn’t for the betterment of anyone. Waukesha has actually somehow managed to turn that trend on its head. They have created an old-fashion feel downtown that you can walk around and shop, eat and even visit a bookstore and if you stay until the sun goes down you will find plenty of live music.

People’s Park fits perfectly in downtown Waukesha as it opened in a historic Downtown landmark building, that offers you multiple floors to dine, including the stunning rooftop, that the only reason not to pick that spot to dine would be if it was covered in snow. The stunning view and fabulous bar make the rooftop a great way to enjoy a weekend brunch or a few cocktails with The Charleston Crab Cakes are so loaded with fresh crab you might just think you are on the east coast and not Wisconsin. You are in Wisconsin so the brat burger would be a great twist on a local favorite with a house-made Pork Bratwurst Patty being the focal point, but it is tastily enhanced with a soft Pretzel Bun and Sauer Kraut. One bit in and you will know why brats are so beloved. The Topanga Canyon chicken brings the flavors of shallots and garlic to the sautéed chicken breasts that come with Portabella Mushrooms in a Wine sauce. Finally the only way to end your meal is with the bourbon bread pudding; this is simply richness upon richness. It starts with house-baked Vanilla Custard Bread Pudding and then it is topped with a Bourbon Vanilla Butter Cream Sauce and a scoop of vanilla frozen custard. People’s Park is quite the eclectic restaurant with a menu to match.

Rooftop View from People’s Park

Burger with Cucumber Salad at People’s Park

While Waukesha has more than enough to fill your vacation schedule, if you visit during the summer you might just want to visit the world’s largest music festival, Summerfest. If you are going, enjoy Waukesha, stop at Goerke’s Corners Park and Ride, right off of I-94, and grab a shuttle that will drop you right at the lakefront and then pick you back up at the end of the night.

Sometimes you don’t know a place is a great vacation spot until you are actually there and Waukesha is just that. It might be a little note on a map and a name you might not know how to pronounce, but one visit and you will find that this city is really what a vacation spot is all about. Charm, warmth, friendliness and experiences that you can’t find anywhere else.

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